


Waking Up with Regret

by supernatural_jackles



Category: Supernatural
Genre: F/M
Language: English
Status: Completed
Published: 2018-12-03
Updated: 2018-12-03
Packaged: 2019-09-06 14:40:40
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,006
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16834606
Author URL: https://archiveofourown.org/users/supernatural_jackles/pseuds/supernatural_jackles
Summary: Can you write a dean x reader where they just got back from a hunt and they sleep together and the next morning Dean finds out it was the readers first time. and can you make it angsty/fluffy please :) ps love your writing





	Waking Up with Regret

**Author's Note:**

> Warnings: angst, fluff, smut

“I can’t believe how well that hunt went!” Dean said cheerfully, “I mean, a hunt actually went as planned, there were only a couple of scrapes and bruises, and no one was killed after we got there.”

“I know, I could settle for that more often,” Sam added.

“Well, time to celebrate,” you walked in with three beers in your hands, handing the boys a beer before taking your seat on the couch next to Dean.

“Very smart, Y/N. So what do you guys want to watch?” Dean asked.

You had been with the Winchesters for years now. You had been captured by a demon when they came in and saved you, patching you up and making sure you were okay. They informed you that you’re parents didn’t make it, since the demon had gone there first to find you. That meant you were on your own. You were lost, you had no family, no friends to support you, only the Winchester’s making sure you were okay. Eventually, they just let you tag along. You started doing research for them, and patching them up when they got hurt. You did a lot for them, you felt the need to repay them for everything they have done for you. Soon enough, they taught you how to fight and defend yourself, hoping that they could use you on a case. Needless to say, you’ve been hunting for about a year now.

You felt like part of the family around them, they always included you in stuff, always protected you even a little too much. They were everything you needed. You became close to Sam at first. He taught you all about research and what exactly to look for. He became your best friend, someone you could share a good laugh with and could trust. He was the person you wish you’d always had in your life.

Dean on the other hand, was a different story. He kept a watchful eye on you when you were healing, constantly making sure you were okay and had everything you needed. He protected you on hunts, always throwing himself in front of the fire in order to make sure you were safe. At first he was a little wary of you, you figured it was because he didn’t know if he could trust you, but as time passed, he learned he needed someone like you. The two of you were best friends who literally did everything together. You shared your food with one another, had the same taste in music; which came in handy when he decided to join you at night and listen to it with you. You talked about things with one another, things you wouldn’t dare share with anyone else, and you knew that Dean wouldn’t dare share, nor would he judge you. The only thing you didn’t talk to him about was relationships and sex, because you never had either one of those, and that would be embarrassing, considering you were in love with him.

He came to you with advice on what girls like, and how to really get a girl to like him, and of course you helped him. You didn’t want him to know about your stupid crush. As much as it hurt you to watch him hit on every busty blonde, it was better than losing your best friend. Also, he liked women with experience, something that you definitely didn’t have which was another reason not to tell him you loved him.

Sam had picked the movie and put it in. Dean threw his arm around your shoulder, bringing you into him. A gesture he did often when you watched movies. You took comfort in having him wrap his around you. It was the closest you were going to get to the real thing. You rested your head under his chin and began to watch the movie.

Sam knew you were in love with his older brother. He could see it in the way you looked at him. It wasn’t hard to figure out. He couldn’t quite understand why you wouldn’t tell him, though he knew you were insecure, and didn’t want to ruin your friendship over something like this. He still supported you, no matter what you did. He comforted you when Dean took off with some other woman. To him, you were his little sister, and he protected you. He hated seeing you hurt.

He also loved to see how happy Dean made you. Whether he was teasing you or simply wrapping his arm around you while you watched a movie, he knew just how happy you were. He knew Dean had a special place for you in his heart. He never shared any of his food with anyone, and he shared everything right down to his pie with you. He opened up to you, let you see the vulnerable side of him, something he swore his brother would never do.

You always enjoyed a good comedy, especially watching it with the boys. The enjoyment of laughing together, at the stupidest things was enough to make you happy. It was the simple things. The way you felt Dean’s body flex as he chuckled, the way you watched Sam throw his head back in laughter, it was music to your ears.

“So, I was thinking that we’d take a few days to relax. You know, catch up on some sleep, eat a proper meal or two. We’ve been hunting nonstop for the past six months,” Dean suggested.

“Alright, I can’t say no to that. I wouldn’t mind catching up on Game of Thrones,” Sam agreed.

“I’m down for it. As long as you’re making your burgers, Dean,” you smiled at him. He let out a chuckle.

“Only for you,” he grinned.

“Okay guys, I’m heading to bed now, I’ll see you both in the morning,” Sam yawned as he got up off of his chair. You stood up and wrapped your arms around him.

“Night, Sammy,” you squeezed him tightly. He placed a kiss to your forehead before walking out of the room.

You sat back down on the couch next to Dean. His arm appearing around your shoulder once more, this time, a little tighter.

“What do you say we watch some Dr Sexy MD? I think I missed a few episodes,” he confessed. You let out a giggle as he changed the channel.

“Sounds good.”

He placed a kiss to your temple, and began to watch the episode. You couldn’t help but curl into him a little more. Relishing in the scent and warmth of his body. He always smelled of some sort of cologne mixed with gunpowder and a little whiskey, in this case it was beer. It was something you loved about him. It always made you feel safe.

“This episode wasn’t as good,” Dean commented.

“Yeah, couldn’t agree more.”

“You did great today, I forgot to tell you that earlier,” he grinned.

“Thanks Dean,” you smiled. “I’m not as good as you or Sam though.”

“Yeah, but you’re still good. You’re a fast learner. You’re getting better, I can see it.”

“Yeah yeah. You’re just trying to make me feel better,” you joked, pushing him lightly.

“No, actually I’m not. Things have definitely gotten better since you got here. Having you around makes things a hell of a lot better,” he said, looking you directly in the eyes. “You’ve definitely helped me out a lot by being here. I mean you’re my best friend.”

“You’re mine too,” you smiled as you wrapped your arms around him. He lifted you onto his lap, so you were straddling his hips, giving him better access to hold you tightly. His arms wrapped around your back, pulling you to his chest, allowing him to bury his head in your neck. Damn did you love this feeling. You felt his fingers ghost over your sides, causing you to flinch slightly. Your movements not going unnoticed by Dean.

“Are you ticklish, Y/N?” he smirked.

“No,” you quickly denied.

“Oh I beg to differ,” he winked.

Suddenly, his fingers were tickling your sides and you squirmed, eliciting a loud bout of laughter from your mouth. He showed no signs of stopping, a wide smile spread over his face as he tickled your midsection. You were laying on your back, him sitting next to you as you begged for him to stop. Tears were springing from your eyes.

“Dean, please!” you laughed, “stop.”

“Never!” he said loudly. His body hovered over you as his fingers continued to dig into you. You did the only thing you could think of, you hoped to god he was ticklish too. You began to tickle his sides, he flinched. Jackpot. “Don’t even think about it, Y/N.”

“Karma’s a bitch, Winchester.” you breathed out.

You continued to drag your fingers over him, his body flinching and squirming as you finally got back at him for the torture he just endured on you.

“Okay, I give. I give. You win!” he yelled. He collapsed on top of you, holding up as much of his weight as he could so he wouldn’t squish you.

His face was very close to yours, you could see how flushed he was. He looked at your with such lust and adoration. Your heart was racing a mile a minute, you hoped to god he couldn’t feel it. He leaned in slowly, giving you an opportunity to back out if you didn’t want to. There is nothing more you wanted. You needed to feel his lips on yours. He brushed the hair away from your face, the sudden contact caused your heart to flutter. His calloused hand cupped your cheek, he smiled before brushing his lips lightly over yours. You were in shock at first, you couldn’t believe he was finally kissing you. You kissed him back, your lips moving slowly with one anothers. His kiss literally taking your breath away.

“Wow,” he breathed out as he pulled away, his forehead pressing to yours.

“Yeah, wow!”

He captured your lips in his once more, this time in a needy kiss. His grip tightened on you as your lips moved in sync with one anothers. His pace changed, he was going slowly, making sure he wasn’t pushing you to go too far. His touch swiftly ran over your bottom lip. It was eye opening at first, but you granted him access. Soon enough, his tongue was exploring your mouth. You were a little timid at first, you didn’t want to overstep any boundaries. You simply glided your tongue over his. He groaned instantly in approval.

You wrapped on your your legs around his waist, his hand immediately coming down to hold it in place. His hips rested on yours, creating the perfect amount of friction, which is exactly what you needed. You ran your fingers through his short hair, stopping at his neck and pulling him closer to you. God you had to be dreaming.

“I think we should take this somewhere else don’t you?” he suggested.

“Good idea.”

He got up off of you and stood up. He held his hand out to you, helping you up with him. He smiled widely before crashing his lips to your once more. He lifted you up instantly, you wrapped your legs around him as he clung to you. You pulled away and began to kiss his jaw line, moving down towards his neck. He walked towards his room as you sucked away at his pulse, making sure to leave your mark on him. You could feel his shoulder muscle flex under your touch.

He kicked the door closed and pressed you against the wall. His lips pressing to yours in a passionate kiss. The way this man kissed did wonders to you. Never in your life had you been kissed the way he kisses you. The way his hands held you tightly, the way his lips moved against yours. The sensation of his tongue dancing with yours. It sent sparks all throughout your body. His touch set fire to your skin, making your heart race in the best way possible.

You could feel his member hardening against your center, the mere thought sending a wave of heat through your body. You could feel your arousal building knowing you were having this kind of affect on him. You experimentally ground your hips against his erection, eliciting a low groan from Dean’s lips. You must have done something right to get that out of him. You did it again, this time, slowly dragging over him. His grip on you tightened as his breathing sped up.

“Sweetheart, you have to stop doing that. You’re going to make me cum before we even start,” he stuttered, causing you to smile.

You boldly took the hem of his shirt, hiking it up his torso to reveal his chest, and his anti-possession tattoo. His hips pinned you to the wall as he lifted his arms above his head, allowing you to remove his shirt completely and discarding it to the floor. His skin was warm and soft, despite the amount of scars spread out over his body. You looked at him in awe before you pressed a soft kiss to his lips. He smiled into the kiss.

“Would it be okay if we took your shirt off too?” he asked kindly. You nodded your head and bit your lip. You were insecure of your body, and you were sure Dean knew about that. You weren’t as thin as you would have liked, and you definitely had some stretch marks that you didn’t want him to see. But you didn’t want this to end; you had to push past it. His fingers carefully lifted the material over your head, leaving you in your bra. You felt his eyes roaming your body and you shut your eyes.

“You’re beautiful,” he whispered as his hand held your hips. His other hand lifting your chin so your gaze would meet his. You could see he meant what he said, and that helped you relax a little.

He held you tightly as he carried you over to his bed. He placed you on the bed, allowing you to move up before he hovered over you once more. His lips were on yours instantly, pulling you in for another passionate kiss. You pulled him into you, wanting to feel his bodyweight on top of you. His one hand travelled over your body, timidly touching your breast through your bra. He sucked your bottom lip into his mouth, gently biting on it before his tongue entered your mouth once more.

His lips moved along your jaw, pressing hard into your skin as he moved down to your neck. He sucked your sensitive skin into his mouth, causing you to bite back your moan. You snaked your hands into his hair as he nipped at your ear.

“Dean,” you begged.

“I’ve got you sweetheart, don’t worry,” he promised. His hot breath trialed over your skin. His hands tracing every inch of your abdomen, trying to learn your body and what you enjoy. You felt his lips between your breasts before he travelled down your stomach, they were hot and wet as he made his way to the waistband of your pajama pants.

“Is this okay?” he asked, “we can stop if you don’t want to.”

“It’s okay, Dean.”

His fingers curled in the waistband of your pants. He removed them from your body, throwing them across the room and stood up, taking the sight of your half naked body on his bed. Even though he couldn’t see any of your intimate parts, you still felt the urge to cover up. You looked at him, your eyes finally getting the chance to see his shirtless form. You could see the bulge in his pants, that was enough to remind you that he wanted you.

“Like what you see?” he winked.

“Definitely,” you replied without thinking, causing him to chuckle.

He pulled you to the edge of the bed before dropping to his knees. He began placing kisses along your exposed legs, growing closer and closer to your heated core. You wanted him more and more every time he moved. You wiggled slightly as he pressed hot wet kisses along the inside of your thighs. His fingers trace over your stretch marks. You flinch away, and he understands why, but chooses not to say anything. He keeps moving, he presses a kiss to your wet panties. His eyes meeting yours, asking for permission.

“Are you okay with this?” he kindly asked.

“Yeah,” you breathed out.

He got up and snaked his arms around your back. You arched your back, allowing him to remove your bra. You managed to roll your hips against his bulge once more as the straps of your bra fell down your arms. Your breasts became exposed to him and instantly you covered up.

“You don’t have to hide from me,” he assured you. “You’re gorgeous.”

He took your hands away from your breasts and smiled. You kept your eyes on him as he dipped down, taking one of your nipples in his warm mouth. The sensation was new to you, but damn did you love it. His tongue ran over the hardening bud. His other hand massaged your breast, gently kneading it as you breathed loudly. You closed your eyes and threw your head back and before you knew it you felt your legs being propped up over his shoulders. He looked at you, asking permission before he trialed your panties down your legs. You were now completely exposed to Dean Winchester.

He placed a kiss to your clit before his fingers brushed over your lips.

“You’re so wet, sweetheart,” he grinned, “I love that this is all for me.”

He rubbed over your clit with his finger a few times before he pushed his middle finger into your center. The sensation was so much better than when you did it on your own. His tongue ran over your clit, causing you to buck against him, letting out a low moan.

He pulled his finger out and licked a long strip along your pussy. He did this several times before he pushed his tongue inside you. His fingers toying at the skin of your inner thighs as he worked his tongue inside of you.

He pushed his finger back inside you and curled it inside of you. His lips sucked at your clit as he brushed over your sweet spot with each movement. You fisted your hand in his hair as you came around his fingers, drawing out a long moan as electricity sprang through your body.

His kissed up your body, capturing your lips in his. You could taste yourself on his tongue. You splay your hand over his chest, wanting nothing more than to have him inside of you.

“Listen, sweetheart as much as I would love to have you go down on me, I don’t think I can wait,” he confessed.

“Okay,” you said. You were secretly thankful that he couldn’t wait. You had never given anyone a blowjob before. It would definitely give away the fact that this was your first time.

He stood up and removed his plaid pajama pants and his boxers in one go. His erection sprang free. The tip leaking with precum. His length and width was impressive, you couldn’t help but think about how that was going to fit. He was big. He took a seat next to you on the bed, removing his socks from his feet.

“Do we need a condom?” he inquired.

“Yeah,” you said shyly.

He reached over to his bedside table, pulling out a foil package and ripping it open. He carefully rolled it over his hard cock before he moved to hover over you. He lined himself up with your entrance, you could feel the tip just outside of you.

“Are you sure you want to do this?” he asked you quietly. “We don’t have to.”

“I’m sure, Dean,” you smiled. He nodded his head and leaned in to kiss you sweetly as he pushed himself slowly inside of you. You felt a slight pain as he grew deeper inside of you and he noticed your discomfort. He stopped immediately.

“Just relax, sweetheart,” he whispered. He kissed you, deeping it to help you try and relax, which was easy after that. He moved as slow as possible and before you knew it, he was fully inside of you. The new sensation was weird, but you liked it.

“You okay?” he asked, concern written on his face.

“Yeah. Can we take this slow?”

“Of course,” he smiled.

His hand came up to cup your cheek as he pulled out almost completely. He pushed back in slowly as his lips met yours. His other hand explored your body, knowing that you liked your hips being touched, he rested it there. You wrapped your arms around his back, pulling him to you. You moved your legs apart a little further as he continued gradually thrusting into you. The dull ache you felt now turning to pleasure.

His lips were now attached to your neck, kiss and sucking away at the skin below your ear.

“You feel so good,” he whispered into your ear.

You wrapped your legs around his ass, allowing to penetrate deeper inside of you. You confidently began to roll your hips to match his pace. His breathing hitches as the two of you move together. You could feel his thrusts pulsate throughout your body. His cock hitting every nerve as he pushed into you. You could feel the fire pooling in your abdomen, you knew you were growing closer.

“Dean, I’m gonna-” you cried out.

“It’s okay, go ahead, I’m right behind you,” he growled.

He quicked the pace, the rhythm of his thrusts changing. The tip of his member hitting your sweet spot with each thrust. You felt as though time was slowing down and everything around you had just stopped except for you and Dean. You were literally surrounded by everything that was him. The coil in your stomach had snapped, you walls came clenching down around Dean as he continued into you. You moaned out his name as you dug your fingers into the hard muscles in his back. His breathing was erratic, soft moans mixed in with his heavy breaths. He held on tightly to your hip as he snaked his arm around your back, clinging onto you for dear life as he came, groaning your name. Everything was white as he helped your ride out your orgasms together.

He lay limp on top of you, calming down from your highs. His lips moved lazily with yours, brushing the hair away from your sweat cover skin. He carefully pulled out of you, discarding the condom into the garbage bin next to his bed before joining you once more.

“You okay?” he asked.

“Yeah, you?”

“Yeah,” he smiled. “That was amazing.”

“Definitely,” you agreed.

He held his arm out for you to move over and cuddle with him, which you gladly accepted. His arm was around you instantly, holding you tightly to his body. You rested your head over his heart, listening to his steady heartbeat as your arm wrapped around his torso.

“Good night, Y/N,” he said as he placed a kiss to your forehead.

“Good night, Dean,” you smiled as you placed a kiss over his heart.

You woke up with a heavy arm around you. You opened your eyes to see Dean asleep, his arm placed safety around you. You still had yours wrapped around his torso and you couldn’t help but smile as you remember what happened last night. Then you remember that this would probably ruin your friendship. You definitely wouldn’t be able to forget this one. You just lay there, content in his arms until you felt him stir beneath you.

“Good morning,” he said, his voice still raspy from sleep.

“Morning,” you smiled. He placed a kiss to your forehead as he turned to his side.

“Last night was fun,” he told you. You were now trying to mentally prepare yourself for what was coming next.

“Yeah it was,” you replied. “We should probably get some breakfast.”

“Sounds good.”

You climbed out of bed, holding the sheet to your body as you threw Dean’s shirt over your body. You reached over and picked up his black boxers and slid them up your legs. He had put on a pair of boxers when you looked over at him.

“So, I don’t know about you, but I definitely think that should happen again,” he said casually.

“Yeah, I agree,” you grinned. “This isn’t going to ruin our friendship though, is it?”

“I don’t see why it should. I mean it’s just two friends, pleasuring each other. It will work, trust me. It’s not the first time I’ve done something like this,” he explained.

“This was my first time,” you said, not realizing what you said. “I mean is my first time-”

“What do you meant this was your first time?” he questioned, slight anger and concern present in his voice.

“Nothing, forget I said anything,” you brushed it off.

“This… this wasn’t your first time was it?” he asked, you stayed silent. “Y/N please tell me that I did not just take your virginity!”

You looked down, you couldn’t meet his eyes. You didn’t want to see the regret on his face. You knew he would regret it. There was no way he would have slept with you if he knew. He would have made up an excuse not to. You quickly composed yourself and made your way out of his room.

You hurried off to your room, closing your door before you buried yourself in your pillows. God how could you have been so stupid? You always got so nervous around him, and last night just made it even worse. Of course you had to let it slip that it was your first time. Now he probably wanted nothing to do with you, and you probably just ruined your friendship with him. Tears spilled down your cheeks for what felt like hours. You were interrupted by a knock at your door.

“Sam, I’m okay. I’m not hungry,” you said. Your voice shaky from your tears.

“Can I come in?” a voice asked, a voice that belonged to Dean. You never replied, in hopes that he would just go away and leave you be. You saw the door open from the corner of your eye, a tall figure entering your dark room and closing the door behind him. “Y/N, can we talk?”

“Sure,” you sniffled. You figured it was probably best to get this over with.

He stepped closer to you, kneeling at the side of the bed before you. It was quiet for a moment, as if he was trying to compose his thoughts.

“Can you look at me?” he asked you kindly, his voice low. You sat up and he moved to situate himself between your legs so he could look at you. He brought his thumb up to your cheek, wiping away a stray tear. “Y/N, I’m so sorry that I reacted the way I did. I know I freaked you out and I’m sorry that I did. I just wish I had know it was your first time. I could have made it special if I would have known, better yet you could have lost it to someone better than me.”

“I’m sorry I didn’t tell you,” you whispered.

“Why didn’t you?”

“Because I knew you wouldn’t have wanted to if you knew. Like you said before, you would have wanted me to lose it to someone better. You don’t like girls with no experience, Dean. You said so on a hunt not too long ago,” you told him.

“Y/N-”

“No, Dean. You don’t get to say those things to me. You have no idea how long I have watched you screw other girls who are way better than me, and hope that one day you’re going to look at me like you want me for once. You don’t know what it’s like to feel so insecure about yourself that you can’t put yourself out there because you’re so afraid. You don’t know how it feels to have the guy you’re in love with, take your virginity, then regret it in the morning because he didn’t know. Dean, you’re the only person I could have ever wanted to lose it too. It’s always been you. Let’s face it Dean, you wouldn’t have wanted to sleep with me last night if you would have known. It was the only time you had ever shown any interest in me as more than a friend and I’m sorry I took the chance,” you explained, wiping your tears with the back of your hand.

“Y/N, if I would have known any of this, I can guarantee you that this would be different,” he told you. He wrapped his arms around you. “I love you so much, Y/N. I really do, and I am glad that I was the one who took your virginity, I just wish I would have known. But I want you to know, I don’t regret last night, not for one second, okay? I don’t, especially now, knowing that I did take it very slow with you and I made sure I treated you right. I’m so sorry that I freaked out.”

“It’s okay, Dean,” you sniffled as you wrapped your arms around him.

“Now, if it’s okay with you, I would definitely like to do that again, but this time I would like to make love to my girlfriend,” he smiled.

“That’s your way of asking me to be your girlfriend?”

“I’m a dork, I know. What do you say?”

“I say, kiss me, boyfriend.”


End file.
